Molecular Recognition via Hydrogen Bonding in Supramolecular Complexes: A Fourier Transform Infrared Spectroscopy Study
Alfonso Martinez-Felipe,
Fraser Brebner,
Daniel Zaton,
Alberto Concellon,
Sara Ahmadi,
Milagros Piñol,
Luis Oriol
Affiliations
Alfonso Martinez-Felipe
Chemical and Materials Engineering Group, School of Engineering, University of Aberdeen, King’s College, Aberdeen AB24 3UE, UK
Fraser Brebner
Chemical and Materials Engineering Group, School of Engineering, University of Aberdeen, King’s College, Aberdeen AB24 3UE, UK
Daniel Zaton
Chemical and Materials Engineering Group, School of Engineering, University of Aberdeen, King’s College, Aberdeen AB24 3UE, UK
Alberto Concellon
Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragoón (ICMA)-Facultad de Ciencias, Universidad de Zaragoza-CSIC, 50009 Zaragoza, Spain
Sara Ahmadi
Department of Chemistry, Firoozabad Branch, Islamic Azad University, 74715-117 Firoozabd, Iran
Milagros Piñol
Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragoón (ICMA)-Facultad de Ciencias, Universidad de Zaragoza-CSIC, 50009 Zaragoza, Spain
Luis Oriol
Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragoón (ICMA)-Facultad de Ciencias, Universidad de Zaragoza-CSIC, 50009 Zaragoza, Spain
We assess the assembly of supramolecular complexes by hydrogen bonding between azocompounds and a diacylaminopyridine monomer by temperature-dependent Fourier transform infrared spectroscopy (FT-IR) and density functional theory (DFT) calculations. The electronic delocalisation in the supramolecular rings formed by multiple hydrogen bonds stabilises the complexes, which coexist with dimeric species in temperature-dependent equilibria. We show how the application of readily available molecular modelling and spectroscopic techniques can predict the stability of new supramolecular entities coexisting in equilibria, ultimately assessing the success of molecular recognition.
